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Contrasting Behavior in the Substitution Reactions of 9‐(2‐Bromomethyl‐6‐methylphenyl)fluorene Rotamers
Author(s) -
Murata Shigeru,
Kanno Seiichiro,
Tanabe Yo,
Nakamura Mikio,
Ōki Michinori
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198106061
Subject(s) - fluorene , conformational isomerism , sn2 reaction , chemistry , substitution reaction , substitution (logic) , stereochemistry , photochemistry , medicinal chemistry , molecule , organic chemistry , philosophy , polymer , linguistics
The rotameric fluorene derivatives sp‐(1) and ap‐(1) exhibit different behavior : in S N 2 reactions the sp ‐form reacts more rapidly than the ap ‐form; on the other hand, in S N 1 reactions— e.g . heating in CF 3 CO 2 H/CHCl 3 , only the sp ‐rotamer participates.